How To Avoid Messaging Mishaps When Working Remotely

Feeling misunderstood all of a sudden? Give this newsletter a read


Welcome to Remotely Inclined, a newsletter about remote work and remote entrepreneurship. If you’d like to sign up, you can do so here. Or just read on…

From conversations with subscribers, it seems a new problem has emerged in the world of forced remote work: communication challenges. When you don’t have body language or situational context to go off of the way you would in an office, there’s a lot of room for misinterpretation and misunderstanding. Even with the right tools in place, effective communication in remote work is different than effective communication in person. 

When I left office life for full-time remote entrepreneurship, I had a hell of a time adjusting to the communication side of things. After a year of doing research and testing different approaches, here’s what helped me communicate more clearly, ensure I was understood, and get my message across whether in verbal or written mediums. 

Here’s what worked for me:

  • In writing

  • In verbal communication

  • In both writing + verbal

In writing

Explain your decision tree

One of the key differences between offices and remote work is time between communications. While you may have meetings or quick chit chats throughout the day in an office, remote work is different. You can message someone, sure, but it’s easier to push off responding for a bit when someone isn’t in front of your face talking to you. 

To get around this issue, anticipate it by communicating downline actions as much as possible. Instead of giving an update about what you’re doing now, explain what you’re doing now and what you’re doing next. 

The reason here is that you’re anticipating gaps in communication. Where you may only give a morning update in an office because you know you’ll be chatting again after lunch, perhaps give a full-day update in a remote environment (if you can) in order to increase your ability to work autonomously. 

Start with your outcome, not your input

In any updates, check ins, or confirmations, start with your outcome and then communicate your inputs. 

I’ve found this helpful for three reasons:

1 - Not everyone will read your whole message

In an outcomes-based remote work environment, you have to share the information in this order: impacting everyone, critical for everyone to know, nice for everyone to know. Your outcomes impact everyone. Your inputs are critical for some to know and nice to have for everyone else. 

2 - Input gaps become clearer when you start with outcomes

If you start with your inputs, you can easily create a logical flow in your mind. But if you start with an outcome and then go to explain inputs, gaps will become clearer. This means you can self-adjust ahead of time or ask for the help you need / hold others to account for their part in the team’s ultimate outcome. 

3 - Starting with an outcome keeps people focused on outcomes

This is especially important at a time of pandemic and panic, where people were not ready or willing to move into this kind forced-remote environment.

In verbal communication

No reference words

When speaking, references make sentences flow nicely. It sounds clunky to constantly repeat yourself and much easier to throw in a “that,” “this,” or “it.” 

In remote work situations, though - especially forced ones where you weren’t expecting it or prepared for it - remove reference words to be more clearly understood. It will sound a bit clunky at first, but it’s crucial. 


“Work on Tasks A and B today then get started on Task C. They should be done by tomorrow as we need to be ready for Tasks C and D to be completed by next Friday.” 

If you said this during a team meeting, you could easily use gesturing, body language, or reading the room to check that you’ve been understood. In a remote setting, there’s a massive possible misunderstanding about what “they” means here. Do you mean Task A needs to be done by tomorrow? A and B? A, B, and C? 

Even if you read this and eye roll, thinking “my people are smarter than that!” I’ve found that it’s not about how smart people are but how much thinking you are asking them to do. A simple change on your part from “they” to a specific reference like “Tasks A and B” would eliminate all confusion, remove all possible misunderstandings, and save the time it would take for someone to eventually ask you to clarify. 

One caveat to this: reference words still make sense if you: 1) Only mentioned one thing in the previous sentence and 2) You are only referring one sentence back. 

Take notes and confirm in writing

Everyone should be taking their own notes and confirming next steps and tasks. While you may also appoint one person to be the official note taker of any meeting, everyone should be taking notes about things pertaining to their work. 

In both writing + verbal communication

“Confirming my understanding, you said…” 

This tactic can feel incredibly pandering and condescending, but I promise you it’s been one of the most effective methods of communicating I’ve ever used. It’s a simple premise: confirm your understanding by reiterating the context, action items, and concerns that someone brought up to you, using your own words. 

This is effective for a few reasons:

  • Repetition is the foundation of learning, so we’re more likely to internalize the communication and remember it. 

  • Repeating it back in real-time gives the other party the chance to correct any small mistakes or assumptions before they become massive.

  • Repetition gives you the chance to use your own words and ways of speaking, which further helps your own understanding of the task and helps the other person learn your communication style.

One time this doesn’t work is in large group meetings. If this is the case, I’d confirm this understanding in an email or in my notes later on, including anyone who may need to give feedback or anyone who gave me deliverables / ideas. 

Do you have a communication tactic that worked for you? Do you have any questions about remote work communication you’d like me to answer? Please don’t hesitate to leave a comment! 

If you know someone who you think would benefit from this newsletter, why not share it with them?